Potential antibacterial agents. Part III. synthesis of 7-oxa-spiro [5, 9] pentadecane - 1, 8, 13 trione: a Novel Macrocyclic lactone

ABSTRACT

In an attempt towards synthesis of intermediates [2a] 2-[1 -cyanoethyl] cyclohexanone, [2b], 2-[1 -nitroethyl] cyclohexanone reaction of morpholinomethyl cyclohexanone hydrochloride with CH3CN [or CH3NO2] was undetaken. Instead of the two intermediates namely 2a, 2b the known compound 3 1 -[1 -oxo-2-hydroxycyclohexyl]-2-[2-oxocyclohexyl]-ethane was obtained. Oxidation of this compound and its LAH reduction product 4 1-[1,2-dihydroxycyclohexyl] -2- [2- hydroxycyclohexyl] ethane with CrO3/Ac OH furnished a hitherto un-described compound 5, oxa-spiro [5,9] -pentadecane-1,8,13 trione. Its structure was established using spectroscopic techniques such as IR, HRIMS 'H-NMR, 13C-NMR etc. Antibacterial activities of the three synthesized compounds have been evaluated